Production of n-substituted derivatives of 1- desoxynojirimicin

C - Chemistry – Metallurgy – 12 – P

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C12P 17/12 (2006.01) C07C 271/16 (2006.01) C07D 211/36 (2006.01) C07D 211/46 (2006.01) C12P 13/00 (2006.01) C12P 19/26 (2006.01)

Patent

CA 1174996

ABSTRACT OF THE DISCLOSURE A process has been developed for the preparation of compounds of the formula (I) Image wherein R is hydrogen or an optionally substituted alkyl radical, which comprises reacting glucose with a compound of the formula H2N-R wherein R has the meaning given above to form a 1-amino-sorbitol of the formula (IV) Image wherein R has the meaning given above, reacting said 1-?rbitol with a compound providing a protective group which can be split off under acid conditions and is stable in the subsequent microbiological oxidation process, aerobically oxidizing the com- pound thus obtained microbiologically to give a protect 6-aminosorbose, splitt- ing off the protective group under acid conditions and hydrogenating the 6-amino- sorbose salt thus obtained with after being isolated or in one operation, to give the compound of the formula (I). The products obtained by the process of the invention are useful as .alpha.-gulcoside inhibitors.

387752

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